Hydrochloric Acid → HCID 21460354, compound

HRID 1941200Notes

Reaction equation

HRID 1941200 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][O:16][CH3:17])[CH:6]=[CH:7][C:8](O)=O.[NH2:18][C:19]1[C:20](=[O:33])[N:21]([CH2:30][CH2:31][CH3:32])[C:22](=[O:29])[N:23]([CH2:26][CH2:27][CH3:28])[C:24]=1[NH2:25].[OH-].[Na+].Cl>O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][O:16][CH3:17])/[CH:6]=[CH:7]/[C:8]1[NH:18][C:19]2[C:20](=[O:33])[N:21]([CH2:30][CH2:31][CH3:32])[C:22](=[O:29])[N:23]([CH2:26][CH2:27][CH3:28])[C:24]=2[N:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedioneHCID 53740252HCID 53740252, compound

Product 1

HCID 21460354HCID 21460354, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Methoxy-4-methoxymethoxy cinnamic acid (4.63 g, 19.4 mmol) and 3-(3-diethylaminopropyl)-1-ethylcarbodiimido hydrochloride (5.08 g) were added to a mixed solution of 4.00 g (17.7 mmol) of 5,6-diamino-1,3-dipropyluracil [J. Med. Chem., 28, 487 (1985)] in 50 ml of dioxane/25 ml of water. The solution was stirred at room temperature for 1 hour while adjusting to pH 5.5. The reaction mixture was cooled to room temperature, then 1.59 g of sodium hydroxide and 2N sodium hydroxide solution (50 ml) were added thereto. The mixture was heated under reflux for 1 hour, followed by cooling. The mixture was neutralized by adding 2N hydrochloric acid and the resulting precipitate was collected by filtration. The obtained crude product was recrystallized from dioxane/water to give 5.06 g (67% yield) of Compound c as pale yellow crystals.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. temperatureby cooling
  5. filtrationthe resulting precipitate was collected by filtration
  6. customThe obtained crude product
  7. customwas recrystallized from dioxane/water

Sources & evidence

ORD record
ord-5171dac954ed49d29bd67183df379b1a
Source dataset
uspto-grants-1997_12
Patent number
US05703085

Reaction notes

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